Reaction #3075

ord-23c1255e56f24480bb48d53be97ec0f6

Reaction equation

Cc1ccc(-c2nnn[nH]2)cc1Br
tetrazole
Cc1ccc(-c2nnn[nH]2)cc1Br
5-(3'-bromo-4'-methylphenyl)tetrazole
C[Si](C)(C)CCOCCl
SEMCl
C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
allyltributyltin
→
C=CCc1cc(-c2nnnn2COCC[Si](C)(C)C)ccc1C
N-trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole

Reactants

Cc1ccc(-c2nnn[nH]2)cc1Br
tetrazole
Cc1ccc(-c2nnn[nH]2)cc1Br
5-(3'-bromo-4'-methylphenyl)tetrazole
C[Si](C)(C)CCOCCl
SEMCl
—
Pd(Ph3)4
C=C[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC
allyltributyltin

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Procedure

A solution of 1.0 mmol of this tetrazole, 2.0 mmol of SEMCl in 10 mL DMF was stirred for 1 h. 2.0 mmol of allyltributyltin and 0.1 mmol of Pd(Ph3)4 was added and heated at 70° C. for 14 h. Chromatography provided N-trimethylsilylethoxymethyl-5-(3'-allyl-4'-methylphenyl)tetrazole.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731432uspto-grants-1998_03